CN87103168A - 取代的嘧啶类化合物 - Google Patents
取代的嘧啶类化合物 Download PDFInfo
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- CN87103168A CN87103168A CN198787103168A CN87103168A CN87103168A CN 87103168 A CN87103168 A CN 87103168A CN 198787103168 A CN198787103168 A CN 198787103168A CN 87103168 A CN87103168 A CN 87103168A CN 87103168 A CN87103168 A CN 87103168A
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
- A01N45/02—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring having three carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
- Y10T428/31649—Ester, halide or nitrile of addition polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Insects & Arthropods (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH177286 | 1986-04-30 | ||
CH1772/86-6 | 1986-04-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN87103168A true CN87103168A (zh) | 1987-12-16 |
Family
ID=4218235
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN198787103168A Pending CN87103168A (zh) | 1986-04-30 | 1987-04-29 | 取代的嘧啶类化合物 |
Country Status (26)
Country | Link |
---|---|
US (1) | US4783468A (ru) |
EP (1) | EP0244360B1 (ru) |
JP (1) | JPH0688981B2 (ru) |
KR (1) | KR870010011A (ru) |
CN (1) | CN87103168A (ru) |
AR (1) | AR247389A1 (ru) |
AT (1) | ATE79614T1 (ru) |
AU (1) | AU598254B2 (ru) |
BR (1) | BR8702106A (ru) |
CA (1) | CA1292231C (ru) |
CS (1) | CS271471B2 (ru) |
DD (1) | DD270907A5 (ru) |
DE (1) | DE3781196D1 (ru) |
DK (3) | DK165690C (ru) |
ES (1) | ES2051771T3 (ru) |
GR (1) | GR3005856T3 (ru) |
HK (1) | HK11694A (ru) |
HU (3) | HU204396B (ru) |
IL (1) | IL82343A0 (ru) |
NZ (1) | NZ220132A (ru) |
PH (1) | PH24337A (ru) |
PT (1) | PT84774B (ru) |
SG (1) | SG135993G (ru) |
SU (2) | SU1657061A3 (ru) |
TR (1) | TR22942A (ru) |
ZA (1) | ZA873082B (ru) |
Cited By (9)
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CN102250017A (zh) * | 2011-06-15 | 2011-11-23 | 扬州天和药业有限公司 | 地昔尼尔的一种合成方法 |
CN102399193A (zh) * | 2011-12-15 | 2012-04-04 | 连云港市亚晖医药化工有限公司 | 4,6-二氨基-2-环丙胺基-5-腈基嘧啶的制备方法 |
CN102612360A (zh) * | 2009-09-21 | 2012-07-25 | 梅里亚有限公司 | 用于预防和治疗动物中的昆虫侵袭的基于环虫腈的水性悬浮液和非-水溶液投放和喷洒制剂 |
CN103416420A (zh) * | 2012-05-18 | 2013-12-04 | 陕西汤普森生物科技有限公司 | 一种含环虫腈的杀虫组合物 |
CN103416430A (zh) * | 2012-05-24 | 2013-12-04 | 陕西汤普森生物科技有限公司 | 一种农药组合物 |
CN103444765A (zh) * | 2012-05-31 | 2013-12-18 | 陕西汤普森生物科技有限公司 | 一种含环虫腈与拟除虫菊酯类的杀虫组合物 |
CN103880759A (zh) * | 2014-01-28 | 2014-06-25 | 东南大学 | 一种地昔尼尔药物晶型ⅰ及其制备方法 |
CN104130197A (zh) * | 2014-07-29 | 2014-11-05 | 华中农业大学 | 2,4,6-三氨基-5-氰基嘧啶的化学合成方法 |
CN104649982A (zh) * | 2015-02-26 | 2015-05-27 | 齐鲁晟华制药有限公司 | 一种地昔尼尔的制备方法 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2941794A (en) * | 1956-04-13 | 1960-06-21 | Geddes Edith Bel | Building structures |
DE59206635D1 (de) * | 1991-04-11 | 1996-08-01 | Lonza Ag | Verfahren zur Herstellung von 4-Amino-2-chlor-5-cyan-6-(methylthio)pyrimidin |
RU95113597A (ru) * | 1992-12-02 | 1997-06-10 | ФМК Корпорейшн (US) | Инсектицидная композиция, способы борьбы с насекомыми |
US5344955A (en) * | 1993-02-19 | 1994-09-06 | Ciba-Geigy Corporation | Preparation of 1-amino-cyan-amido-2,2-dicyanoethylene, sodium salt |
DE4311901A1 (de) * | 1993-04-10 | 1994-10-13 | Huels Chemische Werke Ag | Neue Azeomethine, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
JPH09500632A (ja) * | 1993-07-26 | 1997-01-21 | チバ−ガイギー アクチェンゲゼルシャフト | 置換4,6−ジアミノ−5−シアノピリミジン類の製造方法 |
PT915656E (pt) * | 1996-04-29 | 2003-12-31 | Syngenta Participations Ag | Composicao pesticida |
PT1007516E (pt) * | 1997-08-27 | 2004-11-30 | Novartis Ag | Polimorfos e hidratos de diciclanilo e sua preparacao |
AU2007202548B1 (en) * | 2007-06-01 | 2007-11-01 | Zoetis Services Llc | Pesticide Composition |
EP2262368A1 (en) * | 2008-03-28 | 2010-12-22 | Novartis AG | Dicyclanil formulation |
NZ585222A (en) * | 2009-05-08 | 2011-12-22 | Jurox Pty Ltd | Veterinary composition comprising dicyclanil |
CN102113496B (zh) * | 2010-01-03 | 2013-04-03 | 海利尔药业集团股份有限公司 | 一种含有环虫腈和灭多威的杀虫组合物 |
JP5731205B2 (ja) * | 2011-01-14 | 2015-06-10 | 株式会社エス・ディー・エス バイオテック | 農園芸用の有害生物防除剤としてのピリミジン誘導体 |
JP2015003900A (ja) * | 2013-05-23 | 2015-01-08 | 宮崎みどり製薬株式会社 | ワクモ防除剤 |
PL239600B1 (pl) * | 2018-09-20 | 2021-12-20 | Icb Pharma Tomasz Swietoslawski Pawel Swietoslawski Spolka Jawna | Nowa sól dicyclanilu, sposób otrzymywania takiej soli, kompozycje zawierające taką sól oraz zastosowanie takiej soli do zwalczania i kontrolowania pasożytów, a zwłaszcza larw muchówek |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH376115A (de) * | 1957-12-06 | 1964-03-31 | Ciba Geigy | Verfahren zur Herstellung neuer substituierter Pyrimidine |
CH574206A5 (ru) * | 1972-11-16 | 1976-04-15 | Ciba Geigy Ag | |
GB1523274A (en) * | 1974-08-05 | 1978-08-31 | Ici Ltd | Herbicidal compositions containing substituted pyrimidine |
CA1072556A (en) * | 1976-08-27 | 1980-02-26 | Fmc Corporation | Herbicidal 5-pyrimidinecarbonitriles |
US4092150A (en) * | 1976-08-27 | 1978-05-30 | Fmc Corporation | Herbicidal 5-pyrimidinecarbonitriles |
DD157192A1 (de) * | 1981-03-13 | 1982-10-20 | Rainer Evers | Verfahren zur synthese von 2-funktionalisierten 4-alkylthio-6-amino-pyrimidin-5-carbonitrilen |
CH652396A5 (de) * | 1981-12-07 | 1985-11-15 | Ciba Geigy Ag | Amino-5-nitropyrimidin-derivate. |
DE3205638A1 (de) * | 1982-02-17 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Trisubstituierte pyrimidin-5-carbonsaeuren und deren derivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
-
1987
- 1987-04-22 US US07/041,163 patent/US4783468A/en not_active Expired - Lifetime
- 1987-04-24 EP EP87810262A patent/EP0244360B1/de not_active Expired - Lifetime
- 1987-04-24 DE DE8787810262T patent/DE3781196D1/de not_active Expired - Lifetime
- 1987-04-24 ES ES87810262T patent/ES2051771T3/es not_active Expired - Lifetime
- 1987-04-24 AT AT87810262T patent/ATE79614T1/de not_active IP Right Cessation
- 1987-04-27 IL IL82343A patent/IL82343A0/xx not_active IP Right Cessation
- 1987-04-28 AR AR87307408A patent/AR247389A1/es active
- 1987-04-28 PT PT84774A patent/PT84774B/pt unknown
- 1987-04-28 CA CA000535755A patent/CA1292231C/en not_active Expired - Lifetime
- 1987-04-29 NZ NZ220132A patent/NZ220132A/xx unknown
- 1987-04-29 CN CN198787103168A patent/CN87103168A/zh active Pending
- 1987-04-29 PH PH35196A patent/PH24337A/en unknown
- 1987-04-29 SU SU874202490A patent/SU1657061A3/ru active
- 1987-04-29 BR BR8702106A patent/BR8702106A/pt unknown
- 1987-04-29 ZA ZA873082A patent/ZA873082B/xx unknown
- 1987-04-29 HU HU873977A patent/HU204396B/hu not_active IP Right Cessation
- 1987-04-29 HU HU871953A patent/HU201651B/hu unknown
- 1987-04-29 DK DK217787A patent/DK165690C/da not_active IP Right Cessation
- 1987-04-29 HU HU9203430A patent/HU9203430D0/hu unknown
- 1987-04-29 AU AU72194/87A patent/AU598254B2/en not_active Expired
- 1987-04-29 DD DD87302257A patent/DD270907A5/de not_active IP Right Cessation
- 1987-04-30 CS CS873075A patent/CS271471B2/cs unknown
- 1987-04-30 JP JP62107947A patent/JPH0688981B2/ja not_active Expired - Lifetime
- 1987-04-30 KR KR870004197A patent/KR870010011A/ko not_active Application Discontinuation
- 1987-04-30 TR TR291/87A patent/TR22942A/xx unknown
-
1988
- 1988-06-28 SU SU884355955A patent/SU1711672A3/ru active
-
1992
- 1992-05-12 DK DK92616A patent/DK61692D0/da not_active Application Discontinuation
- 1992-05-12 DK DK92617A patent/DK61792D0/da not_active Application Discontinuation
- 1992-10-01 GR GR920401774T patent/GR3005856T3/el unknown
-
1993
- 1993-12-21 SG SG135993A patent/SG135993G/en unknown
-
1994
- 1994-02-08 HK HK116/94A patent/HK11694A/xx not_active IP Right Cessation
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102612360A (zh) * | 2009-09-21 | 2012-07-25 | 梅里亚有限公司 | 用于预防和治疗动物中的昆虫侵袭的基于环虫腈的水性悬浮液和非-水溶液投放和喷洒制剂 |
CN102250017A (zh) * | 2011-06-15 | 2011-11-23 | 扬州天和药业有限公司 | 地昔尼尔的一种合成方法 |
CN102399193A (zh) * | 2011-12-15 | 2012-04-04 | 连云港市亚晖医药化工有限公司 | 4,6-二氨基-2-环丙胺基-5-腈基嘧啶的制备方法 |
CN103416420B (zh) * | 2012-05-18 | 2015-10-14 | 陕西汤普森生物科技有限公司 | 一种含环虫腈的杀虫组合物 |
CN103416420A (zh) * | 2012-05-18 | 2013-12-04 | 陕西汤普森生物科技有限公司 | 一种含环虫腈的杀虫组合物 |
CN104996453A (zh) * | 2012-05-18 | 2015-10-28 | 陕西汤普森生物科技有限公司 | 一种含环虫腈的杀虫组合物 |
CN104996453B (zh) * | 2012-05-18 | 2018-06-26 | 陕西汤普森生物科技有限公司 | 一种含环虫腈的杀虫组合物 |
CN103416430A (zh) * | 2012-05-24 | 2013-12-04 | 陕西汤普森生物科技有限公司 | 一种农药组合物 |
CN103416430B (zh) * | 2012-05-24 | 2016-01-13 | 陕西汤普森生物科技有限公司 | 一种农药组合物 |
CN103444765A (zh) * | 2012-05-31 | 2013-12-18 | 陕西汤普森生物科技有限公司 | 一种含环虫腈与拟除虫菊酯类的杀虫组合物 |
CN103880759A (zh) * | 2014-01-28 | 2014-06-25 | 东南大学 | 一种地昔尼尔药物晶型ⅰ及其制备方法 |
CN103880759B (zh) * | 2014-01-28 | 2016-04-20 | 东南大学 | 一种地昔尼尔药物晶型ⅰ及其制备方法 |
CN104130197A (zh) * | 2014-07-29 | 2014-11-05 | 华中农业大学 | 2,4,6-三氨基-5-氰基嘧啶的化学合成方法 |
CN104649982A (zh) * | 2015-02-26 | 2015-05-27 | 齐鲁晟华制药有限公司 | 一种地昔尼尔的制备方法 |
CN104649982B (zh) * | 2015-02-26 | 2016-12-07 | 齐鲁晟华制药有限公司 | 一种地昔尼尔的制备方法 |
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